Book cover art for Obliquity
John Kay

Originally an article in the FT, it probably had more value as a single short essay than an entire book; it felt like I was reading the same point over and over again. I quit this book with about 25% left to go. Worth a good read of the first few chapters, but only a skim from there.

A Direct Route Seldom Works

Taking the straight line towards an outcome that we hope to obtain rarely works. We live in a complex and constantly changing world, filled with many things that we don't know.

Taking a more oblique approach usually confers greater benefits and easier achievement of goals. For example, the fastest way to travel West, from the Gulf of Mexico to the Pacific, would be to first go East and travel the Panama canal.


There are three states of happiness:

  1. Momentary - a meal, a sunset, sex
  2. Contentment - a job well done, a feeling of well-being
  3. Eudaimonia - roughly translated as 'human flourishing'

Eudaimonia is of course the most significant. It's a Greek word, somewhat untranslatable, that encompasses a grander sense of feeling like one's potential in life is being achieved.

We often feel a sense of achievement and fulfilment by entering 'flow' states in hobbies and work where we are in inherently uncomfortable and challenging situations.

Running, climbing, raising children, being put under stress to do all manner of things, often leaves us feeling a great deal of happiness and a feeling of being complete.

The direct pursuit of happiness, though, such as through food, drink, sex, drugs may make us happy in the short term but leaves us in far worse position in the long term.


Those that seek profit directly may well get what they want, but not for long. ICI, Boeing, Citigroup and Merck are all companies cited as having either come to ruin or disappeared completely purely because of their decision to look for 'increased shareholder value' or just plain 'growth' instead of building aeroplanes or doing useful things with chemistry.

The route to profit is oblique - it is a reward that follows what you do. It ensues, and it cannot be successfully pursued (for long).

'Shareholder value is the dumbest idea in the world.' - Jack Welch

Wealth and Materialism

The direct pursuit of wealth only ever seems to damage people. Perhaps irreparably. Certainly, they may become wealthy while they do this but the damage is elsewhere.

On the other hand, many of the richest people in the world are not rich because of their pursuit of wealth. Rather, they were interested in making good computers (Gates, Jobs) or good cars (Ford, Musk) and so on and so on.

Lehman Brothers, Salomon Brothers and Bear Stearns (along with all the banks that needed to be bailed out by taxpayer money) are testament to the damaging failure of the pursuit of wealth in the short term and the corresponding damage in the long term.

Objectives, Goals and Actions

The three levels of happiness (momentary, contentment, eudaimonia) map, too, to the levels between high level objectives and the actions we take day to day: 'I am cutting this stone to shape,' versus, 'I am building this cathedral,' versus, 'I am working for the glory of God.'

Your higher level objectives in life can not - should not - be used to constantly define and restrict what you do to certain goals and actions.

Instead, there should be a constantly changing and iterating relationship between them, something that warps and weaves as the world changes around us and as we interact with different events and people within it.

The oblique solution to achieving our goals often requires us to repeatedly reframe the problem time and again, in attempt to make it appear more direct. It asks us to make a good interpretation between the whole and the parts.

The Need for Obliquity

It can feel like we need to have the answers in life. Or it can look like others have those answers (see: all of YouTube and any blog about 'how to do x').

In reality, it is better to just muddle through things. If we take a single-minded approach to life we will likely get fixated on the wrong thing... because the 'thing' will change over time. If we 'muddle' then we are more likely to make small and subtle changes as we go that lead us more efficiently to our goals (which will be changing as well, because we're muddling).


Most problems are incomplete. They are not 'closed' - that is, they are not fully rounded as problems and are imperfectly understood. At least at first. We have to close these problems ourselves and there are just as many bad ways of doing this as there are good ways.

'Closing a problem' requires making a decision or decisions about which information is useful and what isn't. This depends on a variety of things: the context, your skills and abilities, how much information you have in the first place, what others are doing, and so on.

If we try to make decisions using ALL the information available to us - a common mistake - we will probably make the wrong decision because a lot of this information isn't actually useful. Only part of it is.

Are Your a Hedgehog or a Fox?

The Hedgehog approaches life with a singular direction, driven by knowable and certain facts and acting with a univocal attitude. This is an approach that feels more certain and sure and it gains more attention and praise, as a result. Winston Churchill is a good example of this - his singular approach to the Second World War has won him significant praise from many quarters. However, he also managed to cock up a bunch of other political episodes because of that same single-minded approach.

On the other hand, there is The Fox. The Fox takes an oblique approach to all matters and embraces uncertainty because that is the truth of things. They also pay more attention to context, the actions of others and how things change over time. Machiavelli was the archetypal Fox.

The Hedgehog goes through life with 'one big idea'. For The Fox, though? It's complicated, and that's a good thing.

'For reputation, it is often better to fail against the odds than to improve them.'
More of this, but in your inbox.

I write a newsletter about the internet. It's called Internet Connection. There's a few hundred of us that fall down the rabbit hole every other week. Want to come along for the ride? Drop your email below.

Let me read it first